JP3242110B2 - 無作為にエポキシ化した小さな星形ポリマー - Google Patents

無作為にエポキシ化した小さな星形ポリマー

Info

Publication number: JP3242110B2
Authority: JP; Japan
Prior art keywords: polymer; polymers; arm; epoxidized; star
Prior art date: 1992-06-19
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

JP50203394A

Other languages

English (en)

Japanese (ja)

Other versions

JPH07508299A (ja

Inventor

エリツクソン，ジエイムズ・ロバート

デイルマン，ステイーブン・ホワード

ハンドリン，デール・リー，ジユニア

ウイリス，カール・レズリー

サザーランド，ロバート・ジユード

Original Assignee

シエル・インターナシヨナル・リサーチ・マートスハツペイ・ベー・ヴエー

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1992-06-19

Filing date

1993-06-18

Publication date

2001-12-25

1993-06-18 Application filed by シエル・インターナシヨナル・リサーチ・マートスハツペイ・ベー・ヴエー filed Critical シエル・インターナシヨナル・リサーチ・マートスハツペイ・ベー・ヴエー

1995-09-14 Publication of JPH07508299A publication Critical patent/JPH07508299A/ja

2001-12-25 Application granted granted Critical

2001-12-25 Publication of JP3242110B2 publication Critical patent/JP3242110B2/ja

2016-12-25 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

229920000642 polymer Polymers 0.000 title claims description 245
239000000178 monomer Substances 0.000 claims description 50
239000000203 mixture Substances 0.000 claims description 35
150000001993 dienes Chemical class 0.000 claims description 26
-1 olefin epoxides Chemical class 0.000 claims description 17
239000004593 Epoxy Substances 0.000 claims description 10
229920001577 copolymer Polymers 0.000 claims description 10
229920002554 vinyl polymer Polymers 0.000 claims description 8
238000004132 cross linking Methods 0.000 claims description 7
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 7
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 4
239000000565 sealant Substances 0.000 claims description 4
229920001519 homopolymer Polymers 0.000 claims description 3
239000008199 coating composition Substances 0.000 claims description 2
206010073306 Exposure to radiation Diseases 0.000 claims 1
238000010382 chemical cross-linking Methods 0.000 claims 1
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 46
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
229920001195 polyisoprene Polymers 0.000 description 29
238000006735 epoxidation reaction Methods 0.000 description 28
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 26
239000010408 film Substances 0.000 description 25
229920005989 resin Polymers 0.000 description 24
239000011347 resin Substances 0.000 description 24
239000002904 solvent Substances 0.000 description 23
238000001723 curing Methods 0.000 description 20
238000006243 chemical reaction Methods 0.000 description 19
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
230000001070 adhesive effect Effects 0.000 description 18
238000009472 formulation Methods 0.000 description 18
239000000853 adhesive Substances 0.000 description 17
238000000034 method Methods 0.000 description 17
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 16
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
238000005859 coupling reaction Methods 0.000 description 13
150000002118 epoxides Chemical class 0.000 description 13
238000005227 gel permeation chromatography Methods 0.000 description 13
238000006116 polymerization reaction Methods 0.000 description 13
238000012360 testing method Methods 0.000 description 13
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 12
239000000126 substance Substances 0.000 description 12
238000005481 NMR spectroscopy Methods 0.000 description 11
230000008878 coupling Effects 0.000 description 10
238000010168 coupling process Methods 0.000 description 10
238000005984 hydrogenation reaction Methods 0.000 description 10
239000003999 initiator Substances 0.000 description 10
238000002360 preparation method Methods 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000002253 acid Substances 0.000 description 9
WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 9
230000005855 radiation Effects 0.000 description 9
238000003756 stirring Methods 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
238000004519 manufacturing process Methods 0.000 description 8
239000000047 product Substances 0.000 description 8
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 7
239000004820 Pressure-sensitive adhesive Substances 0.000 description 7
150000001412 amines Chemical class 0.000 description 7
238000000149 argon plasma sintering Methods 0.000 description 7
239000003054 catalyst Substances 0.000 description 7
125000000524 functional group Chemical group 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
238000000576 coating method Methods 0.000 description 6
239000007822 coupling agent Substances 0.000 description 6
230000007423 decrease Effects 0.000 description 6
238000010894 electron beam technology Methods 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
229920006267 polyester film Polymers 0.000 description 6
239000000523 sample Substances 0.000 description 6
229920006132 styrene block copolymer Polymers 0.000 description 6
239000005062 Polybutadiene Substances 0.000 description 5
238000010539 anionic addition polymerization reaction Methods 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
239000011521 glass Substances 0.000 description 5
230000009477 glass transition Effects 0.000 description 5
238000005259 measurement Methods 0.000 description 5
238000002156 mixing Methods 0.000 description 5
229920002857 polybutadiene Polymers 0.000 description 5
150000003097 polyterpenes Chemical class 0.000 description 5
238000006467 substitution reaction Methods 0.000 description 5
SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 5
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
239000004793 Polystyrene Substances 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 4
229920005601 base polymer Polymers 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
239000012943 hotmelt Substances 0.000 description 4
229930195733 hydrocarbon Natural products 0.000 description 4
150000002430 hydrocarbons Chemical class 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
239000012948 isocyanate Substances 0.000 description 4
150000002513 isocyanates Chemical class 0.000 description 4
239000000463 material Substances 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000002530 phenolic antioxidant Substances 0.000 description 4
229920002223 polystyrene Polymers 0.000 description 4
238000003847 radiation curing Methods 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
239000001632 sodium acetate Substances 0.000 description 4
235000017281 sodium acetate Nutrition 0.000 description 4
239000000758 substrate Substances 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
125000000129 anionic group Chemical group 0.000 description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
230000008901 benefit Effects 0.000 description 3
MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 3
238000005516 engineering process Methods 0.000 description 3
125000003700 epoxy group Chemical group 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
238000010304 firing Methods 0.000 description 3
230000006870 function Effects 0.000 description 3
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
238000011065 in-situ storage Methods 0.000 description 3
239000012939 laminating adhesive Substances 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
238000006386 neutralization reaction Methods 0.000 description 3
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
230000008569 process Effects 0.000 description 3
241000894007 species Species 0.000 description 3
238000001370 static light scattering Methods 0.000 description 3
PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 3
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
238000004448 titration Methods 0.000 description 3
238000005406 washing Methods 0.000 description 3
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical class C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
229920002799 BoPET Polymers 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
239000005041 Mylar™ Substances 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
239000004952 Polyamide Substances 0.000 description 2
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
238000003848 UV Light-Curing Methods 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
239000010426 asphalt Substances 0.000 description 2
229920001400 block copolymer Polymers 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
239000003729 cation exchange resin Substances 0.000 description 2
125000002091 cationic group Chemical group 0.000 description 2
230000008859 change Effects 0.000 description 2
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
239000000835 fiber Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
150000004820 halides Chemical group 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
125000004356 hydroxy functional group Chemical group O* 0.000 description 2
230000005865 ionizing radiation Effects 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
238000012423 maintenance Methods 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
229910052753 mercury Inorganic materials 0.000 description 2
239000003607 modifier Substances 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
150000004967 organic peroxy acids Chemical class 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
150000004965 peroxy acids Chemical class 0.000 description 2
229920002589 poly(vinylethylene) polymer Polymers 0.000 description 2
229920002647 polyamide Polymers 0.000 description 2
229920000647 polyepoxide Polymers 0.000 description 2
230000000379 polymerizing effect Effects 0.000 description 2
229920000098 polyolefin Polymers 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
238000007639 printing Methods 0.000 description 2
238000012545 processing Methods 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
230000009467 reduction Effects 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000007787 solid Substances 0.000 description 2
150000003440 styrenes Chemical class 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
239000010936 titanium Substances 0.000 description 2
229910052719 titanium Inorganic materials 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
CCEFMUBVSUDRLG-KXUCPTDWSA-N (4R)-limonene 1,2-epoxide Natural products C1[C@H](C(=C)C)CC[C@@]2(C)O[C@H]21 CCEFMUBVSUDRLG-KXUCPTDWSA-N 0.000 description 1
PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
HIACAHMKXQESOV-UHFFFAOYSA-N 1,2-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=CC=C1C(C)=C HIACAHMKXQESOV-UHFFFAOYSA-N 0.000 description 1
PRJNEUBECVAVAG-UHFFFAOYSA-N 1,3-bis(ethenyl)benzene Chemical compound C=CC1=CC=CC(C=C)=C1 PRJNEUBECVAVAG-UHFFFAOYSA-N 0.000 description 1
WEERVPDNCOGWJF-UHFFFAOYSA-N 1,4-bis(ethenyl)benzene Chemical compound C=CC1=CC=C(C=C)C=C1 WEERVPDNCOGWJF-UHFFFAOYSA-N 0.000 description 1
WEEGYLXZBRQIMU-UHFFFAOYSA-N 1,8-cineole Natural products C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 description 1
ILBBNQMSDGAAPF-UHFFFAOYSA-N 1-(6-hydroxy-6-methylcyclohexa-2,4-dien-1-yl)propan-1-one Chemical compound CCC(=O)C1C=CC=CC1(C)O ILBBNQMSDGAAPF-UHFFFAOYSA-N 0.000 description 1
NQFUSWIGRKFAHK-UHFFFAOYSA-N 2,3-epoxypinane Chemical compound CC12OC1CC1C(C)(C)C2C1 NQFUSWIGRKFAHK-UHFFFAOYSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
WWSJZGAPAVMETJ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-ethoxypyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)OCC WWSJZGAPAVMETJ-UHFFFAOYSA-N 0.000 description 1
UVPKUTPZWFHAHY-UHFFFAOYSA-L 2-ethylhexanoate;nickel(2+) Chemical compound [Ni+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O UVPKUTPZWFHAHY-UHFFFAOYSA-L 0.000 description 1
YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
AQWSFUIGRSMCST-UHFFFAOYSA-N 3-pyridin-3-ylsulfonyl-5-(trifluoromethyl)chromen-2-one Chemical compound N1=CC(=CC=C1)S(=O)(=O)C=1C(OC2=CC=CC(=C2C=1)C(F)(F)F)=O AQWSFUIGRSMCST-UHFFFAOYSA-N 0.000 description 1
OCTVDLUSQOJZEK-UHFFFAOYSA-N 4,5-diethylocta-1,3-diene Chemical compound CCCC(CC)C(CC)=CC=C OCTVDLUSQOJZEK-UHFFFAOYSA-N 0.000 description 1
CJSBUWDGPXGFGA-UHFFFAOYSA-N 4-methylpenta-1,3-diene Chemical compound CC(C)=CC=C CJSBUWDGPXGFGA-UHFFFAOYSA-N 0.000 description 1
RBHIUNHSNSQJNG-UHFFFAOYSA-N 6-methyl-3-(2-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2(C)OC2CC1C1(C)CO1 RBHIUNHSNSQJNG-UHFFFAOYSA-N 0.000 description 1
241000963007 Anelosimus may Species 0.000 description 1
IVRMZWNICZWHMI-UHFFFAOYSA-N Azide Chemical compound [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 1
ADAHGVUHKDNLEB-UHFFFAOYSA-N Bis(2,3-epoxycyclopentyl)ether Chemical compound C1CC2OC2C1OC1CCC2OC21 ADAHGVUHKDNLEB-UHFFFAOYSA-N 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
239000007848 Bronsted acid Substances 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
239000004821 Contact adhesive Substances 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
239000004606 Fillers/Extenders Substances 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
239000004831 Hot glue Substances 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical group ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
CCEFMUBVSUDRLG-XNWIYYODSA-N Limonene-1,2-epoxide Chemical compound C1[C@H](C(=C)C)CCC2(C)OC21 CCEFMUBVSUDRLG-XNWIYYODSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
239000004677 Nylon Substances 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
229920001744 Polyaldehyde Polymers 0.000 description 1
229920002732 Polyanhydride Polymers 0.000 description 1
229920002614 Polyether block amide Polymers 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000004721 Polyphenylene oxide Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
241000124033 Salix Species 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000003926 acrylamides Chemical class 0.000 description 1
239000002313 adhesive film Substances 0.000 description 1
125000003172 aldehyde group Chemical group 0.000 description 1
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
229920003180 amino resin Polymers 0.000 description 1
ZHNUHDYFZUAESO-OUBTZVSYSA-N aminoformaldehyde Chemical compound N[13CH]=O ZHNUHDYFZUAESO-OUBTZVSYSA-N 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
229910052787 antimony Inorganic materials 0.000 description 1
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
230000003078 antioxidant effect Effects 0.000 description 1
235000013524 arak Nutrition 0.000 description 1
235000020053 arrack Nutrition 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical compound CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 description 1
XZKRXPZXQLARHH-UHFFFAOYSA-N buta-1,3-dienylbenzene Chemical compound C=CC=CC1=CC=CC=C1 XZKRXPZXQLARHH-UHFFFAOYSA-N 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000004568 cement Substances 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000004581 coalescence Methods 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
239000002131 composite material Substances 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
238000012937 correction Methods 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
239000011243 crosslinked material Substances 0.000 description 1
238000005520 cutting process Methods 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
150000008049 diazo compounds Chemical class 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000013013 elastic material Substances 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
125000006575 electron-withdrawing group Chemical group 0.000 description 1
238000004945 emulsification Methods 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
239000003822 epoxy resin Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
LDLDYFCCDKENPD-UHFFFAOYSA-N ethenylcyclohexane Chemical compound C=CC1CCCCC1 LDLDYFCCDKENPD-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000009459 flexible packaging Methods 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical compound CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 description 1
238000006197 hydroboration reaction Methods 0.000 description 1
238000007037 hydroformylation reaction Methods 0.000 description 1
230000002209 hydrophobic effect Effects 0.000 description 1
230000006872 improvement Effects 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
238000003475 lamination Methods 0.000 description 1
239000010410 layer Substances 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000000944 linseed oil Substances 0.000 description 1
235000021388 linseed oil Nutrition 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910003002 lithium salt Inorganic materials 0.000 description 1
159000000002 lithium salts Chemical class 0.000 description 1
229920002521 macromolecule Polymers 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
238000000691 measurement method Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000012528 membrane Substances 0.000 description 1
150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229920001778 nylon Polymers 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
150000002900 organolithium compounds Chemical class 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
239000002985 plastic film Substances 0.000 description 1
229920006255 plastic film Polymers 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920006149 polyester-amide block copolymer Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001228 polyisocyanate Polymers 0.000 description 1
239000005056 polyisocyanate Substances 0.000 description 1
229920001470 polyketone Polymers 0.000 description 1
229920006254 polymer film Polymers 0.000 description 1
239000003505 polymerization initiator Substances 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
125000000905 polyterpene group Chemical class 0.000 description 1
229920006216 polyvinyl aromatic Polymers 0.000 description 1
239000011148 porous material Substances 0.000 description 1
238000011417 postcuring Methods 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
150000003138 primary alcohols Chemical class 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000012552 review Methods 0.000 description 1
238000000518 rheometry Methods 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
238000005096 rolling process Methods 0.000 description 1
239000005060 rubber Substances 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000010703 silicon Substances 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
229960001922 sodium perborate Drugs 0.000 description 1
YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000010959 steel Substances 0.000 description 1
TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical class S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
QKSQWQOAUQFORH-UHFFFAOYSA-N tert-butyl n-[(2-methylpropan-2-yl)oxycarbonylimino]carbamate Chemical compound CC(C)(C)OC(=O)N=NC(=O)OC(C)(C)C QKSQWQOAUQFORH-UHFFFAOYSA-N 0.000 description 1
HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
239000010409 thin film Substances 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/08—Epoxidation
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/04—Oxidation
- C08C19/06—Epoxidation
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/30—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule
- C08C19/42—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups
- C08C19/44—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups of polymers containing metal atoms exclusively at one or both ends of the skeleton
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
- C08F297/02—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type
- C08F297/04—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type polymerising vinyl aromatic monomers and conjugated dienes
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/04—Reduction, e.g. hydrogenation
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
- C09D163/08—Epoxidised polymerised polyenes
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
- C09J163/08—Epoxidised polymerised polyenes
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S525/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S525/901—Radial block

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
General Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Inorganic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Wood Science & Technology (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Epoxy Resins (AREA)
Sealing Material Composition (AREA)
Adhesives Or Adhesive Processes (AREA)
Graft Or Block Polymers (AREA)
Paints Or Removers (AREA)

JP50203394A 1992-06-19 1993-06-18 無作為にエポキシ化した小さな星形ポリマー Expired - Lifetime JP3242110B2 (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US901,349		1992-06-19
US07/901,349 US5247026A (en)	1992-06-19	1992-06-19	Randomly epoxidized small star polymers
PCT/EP1993/001585 WO1994000499A1 (en)	1992-06-19	1993-06-18	Randomly epoxidized small star polymers

Publications (2)

Publication Number	Publication Date
JPH07508299A JPH07508299A (ja)	1995-09-14
JP3242110B2 true JP3242110B2 (ja)	2001-12-25

Family

ID=25413998

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP50203394A Expired - Lifetime JP3242110B2 (ja)	1992-06-19	1993-06-18	無作為にエポキシ化した小さな星形ポリマー

Country Status (10)

Country	Link
US (2)	US5247026A (pt)
EP (1)	EP0646138B1 (pt)
JP (1)	JP3242110B2 (pt)
KR (1)	KR950702209A (pt)
CN (1)	CN1080294A (pt)
AU (1)	AU676232B2 (pt)
BR (1)	BR9306560A (pt)
CA (1)	CA2138290A1 (pt)
DE (1)	DE69330127T2 (pt)
WO (1)	WO1994000499A1 (pt)

Families Citing this family (49)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5773524A (en) *	1990-01-16	1998-06-30	Mobil Oil Corporation	Epoxidized liquid elastomeric copolymers
US5382604A (en) *	1991-10-07	1995-01-17	Shell Oil Company	Crosslinked epoxy functionalized polydiene block polymers and adhesives
US5358981A (en) *	1992-12-07	1994-10-25	Shell Oil Company	Solvent-free water-based emulsions of anionically polymerized polymers
US5393818A (en) *	1993-04-06	1995-02-28	Shell Oil Company	Solvent-free laminating adhesive composition from epoxidized block polymer
JPH0753630A (ja) *	1993-06-30	1995-02-28	Shell Internatl Res Maatschappij Bv	末端に水酸基を有する液状スターポリマー
US5332783A (en) *	1993-07-12	1994-07-26	Shell Oil Company	Compatible blends of epoxy resins and epoxidized polydienes
USH1786H (en) *	1993-07-12	1999-02-02	Shell Oil Company	Process for radiation cured conjugated diene-vinyl aromatic hydrocarbon block copolymers
USH1517H (en) *	1993-07-12	1996-02-06	Shell Oil Company	Radiation curable printing ink composition
US5496684A (en) *	1993-09-17	1996-03-05	Chase Elastomer Corporation	Photosensitive compositions and elements for flexographic printing
US5496685A (en) *	1993-09-17	1996-03-05	Chase Elastomer Corporation	Photosensitive compositions and elements for flexographic printing
EP0877057B1 (en) *	1993-12-13	2007-05-02	Daicel Chemical Industries, Ltd.	A polyalkylene resin composition containing an epoxy-modified block copolymer
US5466758A (en) *	1994-04-13	1995-11-14	Yoon-Sik; Lee	Process for preparing polystyrenes having β hydroxy group and polyglycol-grafted polystyrenes thereof
US5478885A (en) *	1994-04-15	1995-12-26	Shell Oil Company	Composition of epoxy resin, epoxidized block polydiene and curing agent
CN1080735C (zh) *	1994-04-15	2002-03-13	国际壳牌研究有限公司	增韧的环氧树脂组合物
US5420202A (en) *	1994-04-15	1995-05-30	Shell Oil Company	Epoxidized low viscosity rubber toughening modifiers for cycloaliphatic epoxy resins
US6255364B1 (en)	1994-06-21	2001-07-03	Shell Oil Company	Crosslinkable waterborne dispersions of epoxidized polydiene block copolymers and amino resins
DE69501531T2 (de) *	1994-07-18	1998-05-20	Shell Int Research	Vernetzbare wässrige Dispersionen von hydroxyfunktionellen Dienpolymeren und Aminoharzen
US5499409A (en) *	1994-07-18	1996-03-19	Shell Oil Company	Epoxidized polydiene block polymer with epoxy resins
US5451619A (en) *	1994-08-19	1995-09-19	Shell Oil Company	Asphalt composition containing epoxidized polymers
FR2723953B1 (fr) *	1994-08-25	1996-09-20	Atochem Elf Sa	Amorceur multifonctionnel pour l'obtention de polymeres en etoile par voie anionique, son procede de fabrication, et polymeres en etoile correspondants, leur procede de fabrication et leurs applications
US6525142B1 (en)	1994-10-11	2003-02-25	Kraton Polymers U.S. Llc	Monohydroxylated diene polymers and epoxidized derivatives thereof
US5576388A (en) *	1994-10-11	1996-11-19	Shell Oil Company	Telechelic polymers and heterotelechelic polydiene block polymers with dual cure systems
US5500481A (en) *	1995-05-17	1996-03-19	Shell Oil Company	Compositions containing epoxidized monohydroxylated diene polymers, amino resins, and reactive reinforcement agents
US5461112A (en) *	1994-10-11	1995-10-24	Shell Oil Company	Epoxidized monohydroxylated block polymer, epoxy resin, curing agent and epoxy diluent
US5459200A (en) *	1994-10-11	1995-10-17	Shell Oil Company	Polyurethane coatings and adhesives containing monohydroxylated diene polymers and epoxidized derivatives thereof
TW309535B (pt) *	1994-10-11	1997-07-01	Shell Int Research
US5543472A (en) *	1995-05-16	1996-08-06	Shell Oil Company	Concurrent epoxidation and catalyst residue extraction
US5721316A (en) *	1995-07-12	1998-02-24	Shell Oil Company	Process for incorporation of expoxidized polydienes into epoxy resins
USH1902H (en) *	1995-08-04	2000-10-03	Shell Oil Company	Asymmetric radial polymers with acrylic monomer arms
CN1097610C (zh) *	1995-11-16	2003-01-01	国际壳牌研究有限公司	可交联羟基官能聚二烯烃聚合物涂料组合物和其制备方法
US5773521A (en) *	1995-12-19	1998-06-30	Shell Oil Company	Coupling to produce inside-out star polymers with expanded cores
US5741856A (en) *	1996-02-14	1998-04-21	Shell Oil Company	Chemical curing of expoxidized diene polymers using aromatic anhydride curing agents
US5837749A (en) *	1996-04-26	1998-11-17	Shell Oil Company	Non-aqueous solvent free process for making UV curable adhesives and sealants from epoxidized monohydroxylated diene polymers (III)
US5840814A (en) *	1996-08-07	1998-11-24	The University Of Akron	Multi-arm star polymers having a well-defined core and methods for the synthesis thereof
US5922467A (en) *	1996-10-15	1999-07-13	Shell Oil Company	Method for coating crosslinkable epoxidized monohydroxylated diene polymer coating compositions on primed substrates
US6043316A (en) *	1996-11-13	2000-03-28	Shell Oil Company	Crosslinkable hydroxy terminated polydiene polymer coating compositions for use on substrates and a process for preparing them
US6042943A (en) *	1998-03-23	2000-03-28	Alvin C. Levy & Associates, Inc.	Optical fiber containing a radiation curable primary coating composition
US5985952A (en) *	1998-03-23	1999-11-16	Alvin C. Levy & Associates, Inc.	Radiation curable primary coating composition for an optical fiber
WO2003040218A1 (en) *	2001-11-09	2003-05-15	Polymerat Pty Ltd	Porous polymer films
US6996318B2 (en) *	2002-02-18	2006-02-07	Pirelli & C. S.P.A.	Optical fiber with epoxidized polyolefin based coating
DE102005006282A1 (de) *	2005-02-10	2006-08-24	Henkel Kgaa	Strahlungsvernetzbare Schmelzhaftklebstoffe
CN102089388B (zh)	2008-04-30	2014-09-03	莱特高级沥青系统公司	橡胶改性的沥青膏及其乳液的预处理系统和方法
EP2346940A4 (en)	2008-09-24	2013-04-24	Wright Advanced Asphalt Systems	SYSTEM AND METHOD FOR THE PRODUCTION OF RUBBER-MODIFIED ASPHALT CEMENT HIGH-PERFORMANCE
WO2011018924A1 (ja) *	2009-08-14	2011-02-17	丸善石油化学株式会社	ビニルエーテル系星型ポリマーおよびその製造方法
EP3181596A1 (en) *	2015-12-17	2017-06-21	Lanxess Inc.	Process for epoxidation of unsaturated polymer
EP3181598A1 (en)	2015-12-17	2017-06-21	Lanxess Inc.	Butyl rubber containing allylic alcohol
EP3181595A1 (en)	2015-12-17	2017-06-21	Lanxess Inc.	Treatment of epoxidized unsaturated isoolefin copolymers
AU2019307637B2 (en) *	2018-07-20	2024-12-19	Illumina Cambridge Limited	Resin composition and flow cells incorporating the same
CN116253812B (zh) *	2023-02-17	2025-09-30	北京化工大学	一种耐油耐老化的功能化氢化丁苯橡胶弹性体及其制备和应用

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4051199A (en)	1976-03-04	1977-09-27	Phillips Petroleum Company	Epoxidized copolymers of styrene, butadiene and isoprene

Family Cites Families (33)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1503552A (fr) *	1951-01-28	1967-12-01	Electrochimie Soc	Nouveaux élastomères résistant aux huiles
DE1173658B (de) *	1962-05-11	1964-07-09	Huels Chemische Werke Ag	Verfahren zur Herstellung von fluessigen Epoxypolydiolefinen
DE1251537B (de) *	1965-03-12	1967-10-05	Chemische Werke Hüls Aktienge Seilschaft Marl	Verfahren zur Herstellung von nieder molekularen niedrigviskosen Butadien-/ Diolefm-Copolymeren mit hohem Gehalt an mittelstandigen Doppelbindungen
FR1527043A (fr) *	1967-04-10	1968-05-31	Aquitaine Petrole	Copolymères greffés
US3699184A (en) *	1968-09-12	1972-10-17	Shell Oil Co	Blend of block copolymer, one of which is epoxidized
US3607977A (en) *	1968-09-12	1971-09-21	Shell Oil Co	Block copolymer compositions exhibiting altered surface activity
US3652732A (en) *	1968-11-05	1972-03-28	Exxon Research Engineering Co	Solventless encapsulating block copolymers
GB1294890A (pt) *	1969-12-05	1972-11-01
US3607982A (en) *	1970-06-17	1971-09-21	Shell Oil Co	Hydroxylated block copolymers of butadiene and isoprene
US3743616A (en) *	1971-05-17	1973-07-03	D Kest	Elastomer-based pressure sensitive adhesive composition
US3899474A (en) *	1971-07-05	1975-08-12	Inst Francais Du Petrole	Process for manufacturing hydrogenated polymers from conjugated diolefins
US3970608A (en) *	1974-04-05	1976-07-20	Bridgestone Tire Company Limited	Epoxidized acetylene-conjugated diene random copolymer and the curable composition comprising the same
US4077893A (en) *	1977-05-11	1978-03-07	Shell Oil Company	Star-shaped dispersant viscosity index improver
US4135037A (en) *	1977-06-15	1979-01-16	Phillips Petroleum Company	Adhesives and laminates
US4131725A (en) *	1977-08-08	1978-12-26	Phillips Petroleum Company	Polymer epoxidation process
US4131653A (en) *	1977-09-09	1978-12-26	Phillips Petroleum Company	Epoxidized block copolymers
US4417029A (en) *	1981-08-03	1983-11-22	Atlantic Richfield Company	Derivatization of star-block copolymers
DD219779A1 (de) *	1983-09-05	1985-03-13	Univ Schiller Jena	Verfahren zur epoxidierung von cyclopentadienhaltigen mischpolymerisaten
JPS6142504A (ja) *	1984-08-03	1986-03-01	Kuraray Co Ltd	エポキシ化重合体の製造方法
DE3442200A1 (de) *	1984-11-19	1986-05-28	Henkel KGaA, 4000 Düsseldorf	Lufttrocknendes lackbindemittel auf polybutadienbasis
DD256709A1 (de) *	1984-11-22	1988-05-18	Univ Schiller Jena	Verfahren zur herstellung von epoxidfunktionalisierten polydienen
JPS61136563A (ja) *	1984-12-07	1986-06-24	Toyo Ink Mfg Co Ltd	光硬化型接着性組成物とそれを用いて被着体を接着する方法
JPS61228068A (ja) *	1985-04-01	1986-10-11	Nippon Paint Co Ltd	陰極電着塗料用顔料ペースト
GB8606808D0 (en) *	1986-03-19	1986-04-23	Malaysian Rubber Producers	Elastoplastic compositions
DD249029A1 (de) *	1986-05-05	1987-08-26	Univ Schiller Jena	Verfahren zur herstellung von blockcopolymeren
JPS62257904A (ja) *	1986-05-06	1987-11-10	Nippon Soda Co Ltd	有機スズ基を導入した新規重合体
US4981605A (en) *	1987-06-08	1991-01-01	Mitsui Petrochemical Industries, Ltd.	Liquid modified ethylenic random copolymer and its uses
JPH01115978A (ja) *	1987-10-29	1989-05-09	Asahi Chem Ind Co Ltd	接着剤
US4879349A (en) *	1987-11-05	1989-11-07	Shell Oil Company	Selective hydrogenation process
US5187236A (en) *	1990-01-16	1993-02-16	Mobil Oil Corporation	Solid block and random elastomeric copolymers
GB9007267D0 (en) *	1990-03-30	1990-05-30	Shell Int Research	Process for preparing a dispersant/vi improver
KR100227998B1 (ko) *	1991-04-29	1999-11-01	오노 알버어스	가교-결합 에폭시 관능화 폴리디엔 블럭 중합체, 그들의 제조 방법, 그들을 포함하는 조성물 및 출발 블럭 공중합체
TW226380B (pt) *	1992-04-03	1994-07-11	Shell Internat Res Schappej B V

1992
- 1992-06-19 US US07/901,349 patent/US5247026A/en not_active Expired - Lifetime
1993
- 1993-06-17 CN CN93107186A patent/CN1080294A/zh active Pending
- 1993-06-18 KR KR1019940704616A patent/KR950702209A/ko not_active Withdrawn
- 1993-06-18 AU AU54189/94A patent/AU676232B2/en not_active Ceased
- 1993-06-18 JP JP50203394A patent/JP3242110B2/ja not_active Expired - Lifetime
- 1993-06-18 DE DE69330127T patent/DE69330127T2/de not_active Expired - Lifetime
- 1993-06-18 WO PCT/EP1993/001585 patent/WO1994000499A1/en not_active Ceased
- 1993-06-18 BR BR9306560A patent/BR9306560A/pt not_active Application Discontinuation
- 1993-06-18 EP EP93913024A patent/EP0646138B1/en not_active Expired - Lifetime
- 1993-06-18 CA CA002138290A patent/CA2138290A1/en not_active Abandoned
1994
- 1994-05-03 US US08/237,497 patent/US5428114A/en not_active Expired - Lifetime

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4051199A (en)	1976-03-04	1977-09-27	Phillips Petroleum Company	Epoxidized copolymers of styrene, butadiene and isoprene

Also Published As

Publication number	Publication date
DE69330127T2 (de)	2001-09-27
CN1080294A (zh)	1994-01-05
EP0646138B1 (en)	2001-04-11
US5247026A (en)	1993-09-21
AU676232B2 (en)	1997-03-06
CA2138290A1 (en)	1994-01-06
EP0646138A1 (en)	1995-04-05
US5428114A (en)	1995-06-27
AU5418994A (en)	1994-01-24
WO1994000499A1 (en)	1994-01-06
DE69330127D1 (de)	2001-05-17
JPH07508299A (ja)	1995-09-14
KR950702209A (ko)	1995-06-19
BR9306560A (pt)	1999-01-12

Publication	Publication Date	Title
JP3242110B2 (ja)	2001-12-25	無作為にエポキシ化した小さな星形ポリマー
USH1597H (en)	1996-09-03	Epoxidized diene elastomers for exterior block crosslinking
KR100227998B1 (ko)	1999-11-01	가교-결합 에폭시 관능화 폴리디엔 블럭 중합체, 그들의 제조 방법, 그들을 포함하는 조성물 및 출발 블럭 공중합체
US5229464A (en)	1993-07-20	Epoxidized viscous conjugated diene block copolymers
US5639831A (en)	1997-06-17	Dissimilar arm asymmetric radial or star block copolymers for adhesives and sealants
US5389701A (en)	1995-02-14	Crosslinked adhesive compositions comprising epoxy functionalized polydiene block polymers and hydrogenated tackifying resins
US5399626A (en)	1995-03-21	Viscous conjugated diene block copolymers
US5536772A (en)	1996-07-16	Radiation cured conjugated diene block copolymer compositions
US5686535A (en)	1997-11-11	Viscous conjugated diene block copolymers
JPH10506947A (ja)	1998-07-07	感圧接着剤及びシーラント用硬化性バインダー
US5356993A (en)	1994-10-18	Coreactive conjugated diene polymer compositions which phase separate when cured
JP2000506186A (ja)	2000-05-23	芳香族無水物硬化剤を用いるエポキシ化ジエンポリマーの改良された化学的硬化
EP0832163B1 (en)	1999-03-10	Solvent free process for making uv curable adhesives and sealants from epoxidized monohydroxylated diene polymers
JPH0753649A (ja)	1995-02-28	星形高分子

Legal Events

Date	Code	Title	Description
2004-10-05	R250	Receipt of annual fees	Free format text: JAPANESE INTERMEDIATE CODE: R250
2005-10-11	R250	Receipt of annual fees	Free format text: JAPANESE INTERMEDIATE CODE: R250
2006-10-10	R250	Receipt of annual fees	Free format text: JAPANESE INTERMEDIATE CODE: R250
2007-09-27	FPAY	Renewal fee payment (event date is renewal date of database)	Free format text: PAYMENT UNTIL: 20071019 Year of fee payment: 6
2007-10-09	FPAY	Renewal fee payment (event date is renewal date of database)	Free format text: PAYMENT UNTIL: 20081019 Year of fee payment: 7
2008-10-09	FPAY	Renewal fee payment (event date is renewal date of database)	Free format text: PAYMENT UNTIL: 20081019 Year of fee payment: 7
2008-10-14	FPAY	Renewal fee payment (event date is renewal date of database)	Free format text: PAYMENT UNTIL: 20091019 Year of fee payment: 8
2009-10-15	FPAY	Renewal fee payment (event date is renewal date of database)	Free format text: PAYMENT UNTIL: 20091019 Year of fee payment: 8
2009-10-20	FPAY	Renewal fee payment (event date is renewal date of database)	Free format text: PAYMENT UNTIL: 20101019 Year of fee payment: 9
2010-10-19	FPAY	Renewal fee payment (event date is renewal date of database)	Free format text: PAYMENT UNTIL: 20111019 Year of fee payment: 10
2011-10-18	FPAY	Renewal fee payment (event date is renewal date of database)	Free format text: PAYMENT UNTIL: 20121019 Year of fee payment: 11
2012-10-16	FPAY	Renewal fee payment (event date is renewal date of database)	Free format text: PAYMENT UNTIL: 20131019 Year of fee payment: 12
2013-06-18	EXPY	Cancellation because of completion of term